Wilhelm Sittenthaler

Fungizide Pyridinderivate I: α-Trichlormethyl-3-pyridinmethanole

The title substances, a new type of compounds with fungicidal activity, were synthesized by addition of trichloromethyllithium (and tribromomethyllithium resp.) to various 3-pyridyl ketones at −100°C.

Fungizide Pyridinderivate, 4. Mitt.: α-Trifluormethyl-3-pyridinmethanole

SummaryThe synthesis of a series of the title compounds is described applying the addition of 3-pyridyllithium to appropriate trifluoromethylalkanones (path 1) and addition of lithiumorganyls to 2,2,2-trifluoro-1-(3-pyridyl)-ethanone (path 2), respectively.

Fungizide Pyridinderivate, 2. Mitt.: Derivatisierung von α-Trichlormethyl-3-pyridinmethanol

SummaryThe antifungal lead structure α-trichloromethyl-3-pyridinemethanol (1 a) was modified and esters, (thio-)carbamates, and sulfonates as well as other derivatives incorporating the pyridylcarbinol structure were prepared. The optical resolution as well as the N-oxidation of1 a are described.

Fungizide Pyridinderivate, 3. Mitt.: Unerwarteter Verlauf nukleophiler Substitutionen an einem Pyridinderivat

SummaryIn the course of substitution reactions for the synthesis of new types of fungicides, 3-(1-phenyl-1,2,2,2-tetrachloroethyl)-pyridine (2 c) showed an unexpected substitution behaviour: amino substituents were introduced into the pyridine ring and not into the side-chain.